Role of π–π Stacking and Halogen Bonding by 1,4-Diiodoperchlorobenzene To Organize the Solid State To Achieve a [2 + 2] Cycloaddition Reaction

2019 ◽  
Vol 19 (6) ◽  
pp. 3092-3096 ◽  
Author(s):  
Eric Bosch ◽  
Samantha J. Kruse ◽  
Herman R. Krueger ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding ◽  
Π Stacking

Incorporating Ester Functionality within a Solid-State [2 + 2] Cycloaddition Reaction Based Upon Halogen Bonding Interactions

2020 ◽  
Vol 20 (3) ◽  
pp. 1969-1974 ◽  
Author(s):  
Samantha J. Kruse ◽  
Eric Bosch ◽  
Fayeshun Brown ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding

Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions

CrystEngComm ◽  
2019 ◽  
Vol 21 (43) ◽  
pp. 6671-6675 ◽  
Author(s):  
Eric Bosch ◽  
Samantha J. Kruse ◽  
Eric W. Reinheimer ◽  
Nigam P. Rath ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding

A pair of photoreactive polymorphic co-crystals that undergo a regioselective solid-state [2 + 2] cycloaddition reaction that yields exclusively the head-to-tail photoproduct is reported.

scholarly journals Halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding: origins, current status and discussion

2017 ◽  
Vol 203 ◽  
pp. 485-507 ◽  
Author(s):  
Lee Brammer
Keyword(s):  
Solid State ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Main Group ◽  
Solution Phase ◽  
Current Status ◽  
Solid State Chemistry ◽  
Main Group Elements ◽  
Past Work

The role of the closing lecture in a Faraday Discussion is to summarise the contributions made to the Discussion over the course of the meeting and in so doing capture the main themes that have arisen. This article is based upon my Closing Remarks Lecture at the 203rdFaraday Discussion meeting on Halogen Bonding in Supramolecular and Solid State Chemistry, held in Ottawa, Canada, on 10–12thJuly, 2017. The Discussion included papers on fundamentals and applications of halogen bonding in the solid state and solution phase. Analogous interactions involving main group elements outside group 17 were also examined. In the closing lecture and in this article these contributions have been grouped into the four themes: (a) fundamentals, (b) beyond the halogen bond, (c) characterisation, and (d) applications. The lecture and paper also include a short reflection on past work that has a bearing on the Discussion.

scholarly journals Polyhalides as scaffolds for supramolecular, ion-conducting crown ether stacks

2014 ◽  
Vol 70 (a1) ◽  
pp. C634-C634
Author(s):  
Katharina Fromm ◽  
Aurélien Crochet ◽  
Cyrille Dagri ◽  
Yvens Chérémond
Keyword(s):  
Solid State ◽  
Single Crystal ◽  
Crown Ethers ◽  
Halogen Bonding ◽  
Building Blocks ◽  
Channel Formation ◽  
One Dimensional ◽  
Naoh Solution ◽  
Ion Conducting

"Crown ethers, such as dibenzo-18-crown-6 (DB18C6) are in principle perfect building blocks to be stacked on top of each other for one-dimensional (1D) channel formation. However, in the more than 1000 publications on crown ethers in the solid state, only one case was of channel formation described, but not as main focus of research.[1] We now present a way to systematically induce the stacking of DB18C6 with the help of polyhalides, which play the roles of scaffolds via halogen bonding.[2] These compounds can be considered as ""supramolecular straws"". Using for example potassium as couter ion for triiodide for example, we obtained a solid which contains three differently filled, parallel channels in the solid state, which are arranged between the polyhalide anions. Exchanging potassium with sodium by immersion of a single crystal into NaOH solution leads to a single-crystal-to-single-crystal transformation into a compound with two channel types. This transition from a system crystallizing initially in the P2-space group to yield a compound in Pccn is only possible under these very special conditions. We will further present how the ion transport through these channels can be quantified and which process is involved in ion exchange. The role of the polyhalide anions, which cannot be replaced by other linear anions, will be emphasized as well. "

scholarly journals The role of π–π stacking and hydrogen-bonding interactions in the assembly of a series of isostructural group IIB coordination compounds

2019 ◽  
Vol 75 (2) ◽  
pp. 178-188 ◽  
Author(s):  
Taraneh Hajiashrafi ◽  
Roghayeh Zekriazadeh ◽  
Keith J. Flanagan ◽  
Farnoush Kia ◽  
Antonio Bauzá ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Coordination Compounds ◽  
Spectroscopic Techniques ◽  
Stacking Interactions ◽  
X Ray Crystallography ◽  
Hydrogen Bonding Interactions ◽  
Π Stacking ◽  
Research Domain

The supramolecular chemistry of coordination compounds has become an important research domain of modern inorganic chemistry. Herein, six isostructural group IIB coordination compounds containing a 2-{[(2-methoxyphenyl)imino]methyl}phenol ligand, namely dichloridobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)zinc(II), [ZnCl2(C28H26N2O4)], 1, diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)zinc(II), [ZnI2(C28H26N2O4)], 2, dibromidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)cadmium(II), [CdBr2(C28H26N2O4)], 3, diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)cadmium(II), [CdI2(C28H26N2O4)], 4, dichloridobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)mercury(II), [HgCl2(C28H26N2O4)], 5, and diiodidobis(2-{(E)-[(2-methoxyphenyl)azaniumylidene]methyl}phenolato-κO)mercury(II), [HgI2(C28H26N2O4)], 6, were synthesized and characterized by X-ray crystallography and spectroscopic techniques. All six compounds exhibit an infinite one-dimensional ladder in the solid state governed by the formation of hydrogen-bonding and π–π stacking interactions. The crystal structures of these compounds were studied using geometrical and Hirshfeld surface analyses. They have also been studied using M06-2X/def2-TZVP calculations and Bader's theory of `atoms in molecules'. The energies associated with the interactions, including the contribution of the different forces, have been evaluated. In general, the π–π stacking interactions are stronger than those reported for conventional π–π complexes, which is attributed to the influence of the metal coordination, which is stronger for Zn than either Cd or Hg. The results reported herein might be useful for understanding the solid-state architecture of metal-containing materials that contain M II X 2 subunits and aromatic organic ligands.

Halogen Bonding and π···π Stacking Control Reactivity in the Solid State

2004 ◽  
Vol 126 (14) ◽  
pp. 4500-4501 ◽  
Author(s):  
Tullio Caronna ◽  
Rosalba Liantonio ◽  
Thomas A. Logothetis ◽  
Pierangelo Metrangolo ◽  
Tullio Pilati ◽  
...  
Keyword(s):  
Solid State ◽  
Halogen Bonding ◽  
Π Stacking

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

2018 ◽  
Vol 74 (7) ◽  
pp. 816-829 ◽  
Author(s):  
Hina Andleeb ◽  
Imtiaz Khan ◽  
Antonio Bauzá ◽  
Muhammad Nawaz Tahir ◽  
Jim Simpson ◽  
...  
Keyword(s):  
Solid State ◽  
Density Functional ◽  
Halogen Bond ◽  
Noncovalent Interactions ◽  
Supramolecular Assembly ◽  
Halogen Bonding ◽  
Type I ◽  
Supramolecular Architectures ◽  
Solid State Structures

To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylphenyl 4-methylbenzenesulfonate, C14H12O4S, 3a, 2-formylphenyl 4-chlorobenzenesulfonate, C13H9ClO4S, 3b, 2-formylphenyl 4-bromobenzenesulfonate, C13H9BrO4S, 3c, 4-formylphenyl 4-methylbenzenesulfonate, C14H12O4S, 4a, 4-formylphenyl 4-chlorobenzenesulfonate, 4b, C13H9ClO4S, and 4-formylphenyl 4-bromobenzenesulfonate, C13H9BrO4S, 4c. The title compounds were synthesized under basic conditions from salicylaldehyde/4-hydroxybenzaldehydes and various aryl sulfonyl chlorides. Remarkably, halogen-bonding interactions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding interactions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in molecules' and molecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these interactions. They have been compared to antiparallel π-stacking interactions that are formed between the arylsulfonates.

Unveiling the role of pyrylium frameworks on π-stacking interactions: a combined ab initio and experimental study

2021 ◽  
Author(s):  
Reyes Núñez-Franco ◽  
Gonzalo Jiménez-Osés ◽  
Jesús Jiménez-Barbero ◽  
Francisca Cabrera-Escribano ◽  
Antonio Franconetti
Keyword(s):  
Experimental Study ◽  
Solid State ◽  
Ab Initio ◽  
Stacking Interactions ◽  
Π Stacking

Pyrylium frameworks are excellent π–hole donors in solid state, gas and solution environments.

scholarly journals Halogen bonding stabilizes acis-azobenzene derivative in the solid state: a crystallographic study

2017 ◽  
Vol 73 (2) ◽  
pp. 227-233 ◽  
Author(s):  
Marco Saccone ◽  
Antti Siiskonen ◽  
Franisco Fernandez-Palacio ◽  
Arri Priimagi ◽  
Giancarlo Terraneo ◽  
...  
Keyword(s):  
Solid State ◽  
Density Functional ◽  
Rational Design ◽  
Halogen Bond ◽  
Phase Segregation ◽  
Halogen Bonding ◽  
Density Functional Theory Calculations ◽  
Aliphatic Chain ◽  
Molecular Arrangement

Crystals oftrans- andcis-isomers of a fluorinated azobenzene derivative have been prepared and characterized by single-crystal X-ray diffraction. The presence of F atoms on the aromatic core of the azobenzene increases the lifetime of the metastablecis-isomer, allowing single crystals of thecis-azobenzene to be grown. Structural analysis on thecis-azobenzene, complemented with density functional theory calculations, highlights the active role of the halogen-bond contact (N...I synthon) in promoting the stabilization of thecis-isomer. The presence of a long aliphatic chain on the azobenzene unit induces a phase segregation that stabilizes the molecular arrangement for both thetrans- andcis-isomers. Due to the rarity ofcis-azobenzene crystal structures in the literature, our paper makes a step towards understanding the role of non-covalent interactions in driving the packing of metastable azobenzene isomers. This is expected to be important in the future rational design of solid-state, photoresponsive materials based on halogen bonding.

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